Mike Tyson v Evander Holyfield 1 in Las Vegas, Nevada, 9th November 1996. The first of a sequence of the Tyson knock-down. Holyfield has just connected with a right hook and Tyson is on the canvas. Referee Mitch Halpern counts Tyson who survives the round. (Photo by Michael Brennan/Getty Images)

I am writing this article a few weeks after Andy Ruiz’s performance against Anthony Joshua because I wanted some perspective. Yes, it was a tremendous upset but was it the greatest? The obvious answer is no, that distinction goes to James Douglas and I don’t even think the comparison of the two fights is even close.

Today I want to compare and rate the greatest upsets in all of heavyweight history. The criteria here is simply how big was the upset at the time it happened. Ali is on here a couple of times and to be truthful, knowing what we know now, we could probably relegate those to not being upsets. Let’s face it, they don’t call him “The Greatest” for nothing.

16) Michael Bentt KO 1 Tommy Morrison

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Tommy Morrison four months before this fight had beaten George Foreman to claim the WBO heavyweight title and a fight was looming with Lennox Lewis. Bentt, on the other hand, was a 10-1 undergog and had lost his pro debut to Jerry Jones. The level of competition he had faced gave no indication that he would be able to deal with Morrison. Bentt was a great amateur fighter but so far in his career he had not lived up to expectations. That all changed on this night as he didn’t just beat Morrison, he knocked him out in the first round!

15) James J. Corbett KO 21 John L. Sullivan

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Sullivan was 38-0-1 and was the self-proclaimed baddest SOB around. He had offered a purse of $25,000 and a $10,000 side bet winner-take-all and Corbett and his manager took him up on it. Corbett boxed beautifully the entire fight and slowly wore Sullivan out until round 21 when an exhausted Sullivan was beaten senseless by Corbett, who became the second gloved Heavyweight Champion in history.

14) Gene Tunney UD Jack Dempsey I

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Dempsey and Babe Ruth were the most popular athletes of the roaring ’20s and Dempsey took that fame to heart and fought seldom. It caught up to him in this fight. This is one of those fights where hindsight makes this not look like it’s not so big of an upset. Dempsey had not fought in a little over three years before this and Tunney is an all-time great fighter. Tunney controlled the fight easily, winning in front of over 120,000 fans.

13) Andy Ruiz Jr KO 7 Anthony Joshua

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Ruiz had been a solid pro coming into this fight and most fight fans thought that Joshua was the best heavyweight in the world (he’s not). Ruiz didn’t just land a single punch to win, he repeatedly knocked Joshua down. On this night he was clearly the best fighter, no luck was involved.

12) Corrie Sanders KO 2 Wladimir Klitschko

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Sanders was a relative unknown headed into this fight and Klitschko looked like a man who had the skill could dominate the heavyweight division for the next decade. Sanders exposed Wladimir’s biggest weakness in front of the world, his chin.

11) Ken Norton SD 12 Muhammad Ali I

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Going into this fight Ali was ranked number one and Norton number six. Norton had no standout victories and nobody gave him much of a chance. The surprising thing here is that he actually got the decision! Norton broke Ali’s jaw during the course of the fight and was the definite winner.

10) Muhammad Ali KO 8 George Foreman

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Ali was 32 years old and on the downside of his career, at least that’s what most people thought. Foreman was seemingly invincible, knocking out Joe Frazier in two rounds. It seemed the same fate would await Ali. Ali employed a rope a dope tactic to tire out Foreman and eventually knocked out Foreman in the eighth round of a classic and unforgettable battle.

9) Cassius Clay KO 7 Sonny Liston I

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Once again Ali faced what was considered an invincible opponent and once again Ali showed everybody that nobody was invincible. Ali may have won the fight mentally before it even began, as he acted like a crazy man in the lead up to the fight. During the fight he showed speed no heavyweight has ever shown, even to this day.

8) Hasim Rahman KO5 Lennox Lewis

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Lewis was coming off a dominant performance against the tough David Tua and looked to be at the height of his powers. Rahman was a good fighter with a strong punch but was widely seen as soon-to-be knockout victim. Lewis came into the fight at his highest weight up to that time and got flattened by a stunning right hand near the end of the fifth round.

7) Leon Spinks SD 15 Muhammad Ali

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Spinks was in just his eighth pro bout and just two fights before had struggled to get a draw with Scott LeDoux in a fight most thought LeDoux had won. Ali was older and slower but he had enough to beat the tough Earnie Shavers just a few months before. Ali tried a little rope a dope against Spinks but Spinks was just too strong and kept coming after Ali. As Ali would say after the fight, Spinks was relentless on the attack.

6) Michael Spinks UD 15 Larry Holmes

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No Light Heavyweight Champion had ever beaten the Heavyweight Champion. To make the upset even better, Holmes was just one win away from Rocky Marciano’s 49-0. In three months Spinks gained over twenty pounds under the guidance of nutritionist Mackie Shilstone. Whatever Shilstone did at the training table and in their workouts worked as Spinks constantly beat Holmes to the punch to win a close but deserved decision.

5) James Braddock UD 15 Max Baer

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The bout was held at the Madison Square Garden Bowl, which was nicknamed “The Graveyard of Champions” because no reigning champion had ever successfully defended his title there. And to the surprise of most in attendance, the Graveyard of Champions would bury another one. Baer was seemingly disinterested in fighting on this night and Braddock took full advantage to win a close but just decision.

4) Evander Holyfield KO 11 Mike Tyson I

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People forget going into this fight that Tyson was on a roll and Holyfield had looked old in his last four fights while winning just two of them. Tyson at the opening of betting was a 25-1 favorite which was bet down to 10-1 by fight time. Holyfield, in the end, was just the stronger fighter physically, and more importantly, mentally.

3) Oliver McCall KO 2 Lennox Lewis 

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McCall was a hot and cold heavyweight who had some good wins but also some bad losses. Lewis seemed almost unbeatable going into this fight. He was young, strong and fast. Younger, stronger, and faster, in the end, was not enough because McCall landed a huge right hand that stopped Lewis in the second round.

2) Max Schmeling KO 11 Joe Louis

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Max was the former Heavyweight Champion of the World, but the odds were still over 10-1 against him as he faced the young “Brown Bomber” who had knocked out former Champions Primo Carnera and Max Baer. Schmeling was considered old and over the hill, but he said he saw a weakness in Louis, and he did! He dropped Louis in the 4th round and could barely miss with his right hand afterwards, stopping Louis in the 12th.

1) James Douglas KO 10 Mike Tyson

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This fight is number one and it’s not even close! Tyson was a 42-1 favorite and had been quickly dispatching everything that got in his way, while “Buster” had quit against Tony Tucker and most questioned how much heart Douglas had. On one February night in Tokyo, Japan though, Buster Douglas was special and dominated Tyson for the majority of the fight, finally leaving Tyson on the canvas searching for his mouthpiece a beaten fighter.